Ethanol → Triethyl ethane-1,1,2-tricarboxylate
Reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].C(O)C.CC[O-].[Na+].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>O>[CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])([C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
12 ml of diethyl malonate were introduced into 120 ml of ethanol and then 5.5 grams of sodium ethylate at 98% were added over 10 minutes at 0° to +5° C. The mixture was stirred for 15 minutes at 0°+5° C. and then 8.8 ml of ethyl bromoacetate were added over 30 minutes. The mixture was stirred for 48 hours at ambient temperature and then the mixture was poured into 600 ml of water and extracted 3 times with 300 ml of methylene chloride. The organic phase was washed twice with 300 ml of water, then evaporated to dryness. The oil obtained was distilled under reduced pressure to obtain 12.4 grams of the expected product with a boiling point of 110° to 120° C. at 1.0 mm of Hg.
Workup
- stirringThe mixture was stirred for 48 hours at ambient temperature
- extractionextracted 3 times with 300 ml of methylene chloride
- washThe organic phase was washed twice with 300 ml of water
- customevaporated to dryness
- customThe oil obtained
- distillationwas distilled under reduced pressure
Sources & evidence
- ORD record
- ord-842fb09c51514e72b7fbc17919df7499
- Source dataset
- uspto-grants-1995_12
- Patent number
- US05474996
Reaction notes
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